Hydrazine hydrate (1:1) → 4-(3-Aminopropyl)benzonitrile

HRID 485280Notes

Reaction equation

HRID 485280 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)C(=O)C2=CC=CC=C12.O.NN>CO>[NH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]#[N:14])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 134213034-(3-Phthalimidopropyl)benzonitrile

Product 1

HCID 134213044-(3-Aminopropyl)benzonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 10 g (30 mmols) portion of 4-(3-phthalimidopropyl)benzonitrile were added 1.89 ml (39 mmols) of hydrazine hydrate and 130 ml of methanol, and the mixture was refluxed for 3 hours, cooled to room temperature and then concentrated. The residue was dissolved in 200 ml of 1 mol dm-3NaOH, followed by extraction with ether. The extract was dried over K2CO3 and concentrated, giving 4.32 g (yield 90%) of 4-(3-aminopropyl)benzonitrile.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in 200 ml of 1 mol dm-3NaOH
  4. extractionfollowed by extraction with ether
  5. dry with materialThe extract was dried over K2CO3
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e14c5c136b2245fa8e3ede6d768d5f36
Source dataset
uspto-grants-1985_08
Patent number
US04536391

Reaction notes

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